Chemistry and Biology of Reactive Species
Prof. Harinath Chakrapani Lab
Home > Publications
2025
PUBLICATIONS
2019
Carbonyl Sulfide (COS) Donor Induced Protein Persulfidation Protects against Oxidative Stress
Preeti Chauhan, Kavya Gupta, Govindan Ravikumar, Deepak Saini, and
Harinath Chakrapani*
Chem.Asian J. 2019, 14, 4717 –4724
Chemoproteomics of an Indole-Based Quinone Epoxide Identifies Druggable Vulnerabilities in Vancomycin-Resistant Staphylococcus aureus
Amogh Kulkarni, Isha Soni, Dhanashree S. Kelkar, Allimuthu T. Dharmaraja, Rathinam K. Sankar, Gaurav Beniwal, Abinaya Rajendran, Sharvari Tamhankar, Sidharth Chopra, Siddhesh S. Kamat, and Harinath Chakrapani*
J. Med. Chem. 2019, 62, 6785−6795
Targeted Antibacterial Activity Guided by Bacteria-Specific Nitroreductase Catalytic Activation to Produce Ciprofloxacin
Kundansingh A. Pardeshi, T. Anand Kumar, Govindan Ravikumar, Manjulika Shukla,
Grace Kaul, Sidharth Chopra, and Harinath Chakrapani*
Bioconjugate Chem. 2019, 30, 751−759
Photocontrolled endogenous reactive oxygen species (ROS) generation
Ajay Kumar Sharma, Harshit Singh, and Harinath Chakrapani *
Chem. Commun., 2019, 55, 5259-5262
A chemical–genetic screen identifies ABHD12 as an oxidized-phosphatidylserine lipase
Dhanashree S. Kelkar, Govindan Ravikumar, Neelay Mehendale, Shubham Singh, Alaumy Joshi , Ajay Kumar Sharma , Amol Mhetre , Abinaya Rajendran , Harinath Chakrapani , and Siddhesh S. Kamat
Nature Chemical Biology, 2019, 15, 169–178
2019
2018
A Vinyl-Boronate Ester-Based Persulfide Donor Controllable by Hydrogen Peroxide, a Reactive Oxygen Species (ROS)
Prerona Bora, Preeti Chauhan, Suman Manna, and Harinath Chakrapani*
Org. Lett. 2018, 20, 7916−7920
Redox‐guided small molecule antimycobacterials
Amogh Kulkarni, Ajay Kumar Sharma, and Harinath Chakrapani*
IUBMB Life 2018, 70, 826-835 (Invited Review, Special Issue on New Advances in Tuberculosis Drug Discovery and Therapy)
Reactive Oxygen Species-Triggered Tunable Hydrogen Sulfide Release
Preeti Chauhan, Swetha Jos, and Harinath Chakrapani*
Org. Lett. 2018, 20, 3766−3770
Visible-Light Controlled Release of a Fluoroquinolone Antibiotic for Antimicrobial Photopharmacology
Pooja Kumari, Amogh Kulkarni, Ajay Kumar Sharma, and Harinath Chakrapani*
ACS Omega 2018, 3, 2155−2160
Small molecule generators of biologically reactive sulfur species
Prerona Bora , Preeti Chauhan , Kundansingh A. Pardeshi, and Harinath Chakrapani*
RSC Adv., 2018, 8, 27359-27374
2018
Esterase Sensitive Self-Immolative Sulfur Dioxide Donors
Kundansingh A. Pardeshi, Govindan Ravikumar, and Harinath Chakrapani*
Org. Lett. 2018, 20, 4−7
2018
Visible-Light-Triggered Uncaging of Carbonyl Sulfide for Hydrogen Sulfide (H2S) Release
Ajay Kumar Sharma, Mrutyunjay Nair, Preeti Chauhan, Kavya Gupta,Deepak K Saini, and Harinath Chakrapani*
Org. Lett. 2017, 19, 4822−4825
2018
FLUORO/NO: A Nitric Oxide Donor with a Fluorescence Reporter
Govindan Ravikumar, Meisam Bagheri, Dr. Deepak Kumar Saini, and Dr. Harinath Chakrapani*
ChemBioChem2017, 18, 1529 –1534
2018
A small molecule for theraNOstic targeting of cancer cells
Govindan Ravikumar, Meisam Bagheri, Deepak Kumar Saini, and Harinath Chakrapani*
Chem. Commun., 2017, 53, 13352-13355
2018
Synergistic Activities of Nitric Oxide and Various Drugs
Govindan Ravikumar and Harinath Chakrapani*
Novel Biomedical Applications and Perspectives, 2017, Pages 293-312
2018
“On demand” redox buffering by H2S contributes to antibiotic resistance revealed by a bacteria-specific H2S donor
Prashant Shukla, Vinayak S. Khodade, Mallojjala SharathChandra, Preeti Chauhan, Saurabh Mishra, Shivakumara Siddaramappa, Bulagonda Eswarappa Pradeep, Amit Singh and Harinath Chakrapani*
Chem. Sci., 2017, 8, 4967–4972
2016
2018
Esterase Activated Carbonyl Sulfide/Hydrogen Sulfide (H2S) Donors
Preeti Chauhan, Prerona Bora, Govindan Ravikumar, Swetha Jos, and Harinath Chakrapani*
Org. Lett. 2017, 19, 62−65
2018
A Small Molecule for Controlled Generation of Peroxynitrite
Org. Lett. 2016, 18, 1274−1277
2015
2018
Mycobacterium tuberculosis has diminished capacity to counteract redox stress induced by elevated levels of endogenous superoxide
Free Radical Biology and Medicine, 84, 344-354
2018
Thiol activated prodrugs of sulfur dioxide (SO2) as MRSA inhibitors
Kundansingh A. Pardeshi, Satish R. Malwal, Ankita Banerjee, Surobhi Lahiri, Radha Rangarajan and Harinath Chakrapani*
2018
Benzosulfones as photochemically activated sulfur dioxide (SO2) donors
Satish R. Malwal and Harinath Chakrapani *
Org. Biomol. Chem., 2015, 13, 2399-2406
2014
2018
Site-directed delivery of nitric oxide to cancers
Nitric Oxide 2014, 43, 8−16
2018
Substituent Effects on Reactive Oxygen Species (ROS) Generation by Hydroquinones
Allimuthu T. Dharmaraja, Charu Jain, and Harinath Chakrapani*
J. Org. Chem. 2014, 79, 9413-9417
2018
Bioreductively Activated Reactive Oxygen Species (ROS) Generators as MRSA Inhibitors
Vinayak S. Khodade, Mallojjala Sharath Chandra, Ankita Banerjee, Surobhi Lahiri, Mallikarjuna Pulipeta, Radha Rangarajan, and Harinath Chakrapani*
ACS Med. Chem. Lett. 2014, 5, 7, 777–781
2018
Arylboronate Ester Based Diazeniumdiolates (BORO/NO), a Class of Hydrogen Peroxide Inducible Nitric Oxide (NO) Donors
Allimuthu T. Dharmaraja, Govindan Ravikumar, and Harinath Chakrapani*
Org. Lett. 2014, 16, 10, 2610-2613
2018
A phenacrylate scaffold for tunable thiol activation and release
Rathinam K. Sankar, Rohan S. Kumbhare, Allimuthu T. Dharmarajaa and Harinath Chakrapani*
Chem. Commun., 2014,50, 15323-15326
2018
A highly selective sulfinate ester probe for thiol bioimaging
Satish R. Malwal, Ajay Labade, Abhijeet S. Andhalkar, Kundan Senguptaa and Harinath Chakrapani*
Chem. Commun., 2014,50, 11533-11535
2013
2018
A Small Molecule for Controlled Generation of Reactive Oxygen Species (ROS)
Allimuthu T. Dharmaraja, and Harinath Chakrapani*
Org. Lett. 2014, 16, 2, 398-401
2018
Nitroreductase-activated nitric oxide (NO) prodrugs
2018
INDQ/NO, a Bioreductively Activated Nitric Oxide Prodrug
Kavita Sharma, Aishwarya Iyer, Kundan Sengupta, and Harinath Chakrapani*
Org. Lett. 2013, 15, 2636-2639
2018
Ryan J Holland, Anna E Maciag, Joseph E Saavedra, Larry K Keefer, and Harinath Chakrapani*
Journal of Chemical Crystallography, 2013, 43, 123–126
2018
Benzosultines as Sulfur Dioxide (SO2) Donors
Satish R. Malwal, Mahesh Gudem, Anirban Hazra,* and Harinath Chakrapani*
Org. Lett. 2013, 5, 1116-1119
2012
2018
Cross-Linking Protein Glutathionylation Mediated by O2-Arylated Bis-Diazeniumdiolate “Double JS-K”
Ryan J. Holland*, Anna E. Maciag, Varun Kumar, Lei Shi, Joseph E. Saavedra, Robert K. Prud'homme, Harinath Chakrapani, and Larry K. Keefer
Chem. Res. Toxicol. 2012, 25, 2670-2677
2018
Bioreductively-Activated Prodrugs of Nitric Oxide (NO)
Harinath Chakrapani, and Kavita Sharma
Free Radical Biology and Medicine, 2012, 53, S179
2018
Synthesis, reactive oxygen species generation and copper-mediated nuclease activity profiles of 2-aryl-3-amino-1,4-naphthoquinones
Vinayak S. Khodade, Allimuthu T. Dharmaraja, Harinath Chakrapani*
Bioorganic & Medicinal Chemistry Letters, 2012, 3766-3769
2018
Synthesis and antimycobacterial activity of prodrugs of sulfur dioxide (SO2)
Satish R. Malwal, Dharmarajan Sriram, Perumal Yogeeswari, and Harinath Chakrapani*
2018
Design, synthesis and evaluation of small molecule reactive oxygen species generators as selective Mycobacterium tuberculosis inhibitors
AT Dharmaraja, Alvala, Sriram, Yogeeswari, Chakrapani*
Chem. Commun., 2012, 48, 10325–10327
2018
Synthesis, thiol-mediated reactive oxygen species generation profiles and anti-proliferative activities of 2,3-epoxy-1,4-naphthoquinones
Med. Chem. Commun., 2012, 3, 219
2012
2018
Design, Synthesis, and Evaluation of Thiol-Activated Sources of Sulfur Dioxide (SO2) as Antimycobacterial Agents
Satish R. Malwal, Dharmarajan Sriram, Perumal Yogeeswari, V. Badireenath Konkimalla, and Harinath Chakrapani*
J. Med. Chem. 2012, 55, 553-557
PhD and Post-doc Publications of Dr. Harinath Chakrapani
1) Holland, R.; Maciag, A. E.; Kumar, V.; Shi, L.; Saavedra, J. E.; Prud'homme, R.; Chakrapani, H.; Keefer, L. K. “Crosslinking Protein Glutathionylation Mediated by O2-Arylated Bis-Diazeniumdiolate "Double JS-K"” Chemical Research in Toxicology, 2012, 25, 2670-2677.
2) Deschamps, J. R.; Saavedra, J. E. Cao, Z.; Keefer, L. K.; Chakrapani, H. “Stereochemical Origins of Chromophore Extension in O2-Substituted Diazeniumdiolates, Prodrugs of Nitric Oxide” Journal of Chemical Crystallography, 2013, 43, 123-126.
3) Maciag, A. E.; Holand, R. J.; Saavedra, J. E.; Chakrapani, H.; Shami, P. J.; Keefer, L. K. “Thiol Modification By Pharmacologically Active Agents of the Diazeniumdiolate Class” Forum on Immunopathological Diseases and Therapeutics 2012, 3, 91-95.
4) Maciag, A. E.; Nandurdikar, R. S.; Hong, S. Y.; Chakrapani, H.; Morris, N. L.; Diwan, B.; Shami, P. J.; Shiao, Y-H.; Anderson, L. M.; Keefer, L. K.; Saavedra, J. E. “Activation of the c-Jun N-terminal Kinase /Activating Transcription Factor 3 (ATF3) Pathway Characterizes Effective Arylated Diazeniumdiolate-Based Nitric Oxide-Releasing Anticancer Prodrugs” Journal of Medicinal Chemistry 2011, 54, 7751-7758.
5) Hong, S. Y.; Borchert, G. L.; Maciag, A. E.; Nandurdikar, R. S.; Saavedra, J. E.; Keefer, L. K.; Phang, J. M.; Chakrapani, H. “The Nitric Oxide Prodrug V-PROLI/NO Inhibits Cellular Uptake of Proline” ACS Medicinal Chemistry Letters, 2010, 1, 386–389.
6) Kumar, V.; Hong, S. Y.; Maciag, A. E.; Saavedra, J. E.; Adamson, D.; Prud'homme, R.; Keefer, L. K.; Chakrapani, H. "Stabilization of the Nitric Oxide (NO) Prodrugs and Anti-Cancer Leads, PABA/NO and Double JS-K through Incorporation into PEG-Protected Nanoparticles" Molecular Pharmaceutics 2010, 7, 291-298.
7) Nandurdikar, R. S.; Maciag, A. E.; Hong, S. Y.; Chakrapani, H.; Citro, M. L.; Keefer, L. K.; Saavedra, J. E. "Glycosylated PROLI/NO Derivatives as Nitric Oxide Prodrugs" Organic Letters, 2010, 12, 56–59.
8) Maciag, A. E.; Chakrapani, H.; Saavedra, J. E.; Morris, N. L.; Holland, R. J.; Kosak, K. M.; Shami, P. J.; Anderson, L. M.; Keefer, L. K.“The Nitric Oxide Prodrug JS-K is Effective Against Non-small Cell Lung Cancer Cells in vitro and in vivo : Involvement of Reactive Oxygen Species” Journal of Pharmacology and Experimental Therapeutics 2011, 336, 313-320.
9) Rai, G.; Sayed, A. A.; Lea, W. A.; Luecke, H.; Chakrapani, H.; Prast-Nielsen, S.; Jadhav, A.; Leister, W.; Shen, M.; Inglese, J.; Austin, C. P.; Keefer, L. K.; Arnér, E. S. J.; Simeonov, A.; Maloney, D. J. Williams, D. L.; Thomas, C. J. "Structure-Mechanism Insights and the Role of Nitric Oxide Donation Guide the Development of Oxadiazole-2-Oxides as Therapeutic Agents against Schistosomiasis" Journal of Medicinal Chemistry 2009, 52, 6474-6483.
10) Maciag, A. E.; Saavedra, J. E.; Chakrapani, H. "The Nitric Oxide Prodrug JS-K and its Structural Analogues as Cancer Therapeutic Agents" Anti-Cancer Agents in Medicinal Chemistry 2009, 9, 798-803.
11) Hong, S. Y.; Nandurdikar, R. S.; Saavedra, J. E.; Keefer, L. K.; Chakrapani, H."An improved synthesis of V-PROLI/NO, a cytochrome P450-activated nitric oxide prodrug" Tetrahedron Letters 2009, 50, 4545-4548.
12) Nandurdikar, R. S.; Maciag, A. E.; Citro, M. L.; Shami, P. J.; Keefer, L. K.; Saavedra, J. E.; Chakrapani, H. "Piperazine and homopiperazine analogues of JS-K, an anti-cancer lead compound" Bioorganic and Medicinal Chemistry Letters 2009, 19, 2760-2762.
13) Hong, S. Y.; Saavedra, J. E.; Keefer, L. K.; Chakrapani, H. "Improved Synthesis of V-PYRRO/NO, a Liver-Selective Nitric Oxide Prodrug" Tetrahedron Letters 2009, 50, 2069-2071.
14) Chakrapani, H.; Bartberger, M. D.; Toone, E. J. "C-Nitroso donors of Nitric Oxide" The Journal of Organic Chemistry 2009, 74, 1450-1453.
15) Andrei, D. A.; Maciag, A. E.; Chakrapani, H.; Citro, M. L.; Keefer, L. K.; Saavedra, J. E. " Aryl-bis(Diazeniumdiolates): Potent Inducers of S-Glutathionylation of Cellular Proteins and Their in Vitro Anti-proliferative Activities" Journal of Medicinal Chemistry 2008, 51, 7944-7952.
16) Chakrapani, H.; Maciag, A. E.; Citro, M. L.; Keefer, L. K.; Saavedra, J. E. "Cell-permeable Esters of Diazeniumdiolate Nitric oxide Prodrugs" Organic Letters 2008, 10, 5155-5158.
17) Chakrapani, H.; Kalathur, R. C.; Maciag, A. E.; Citro, M. L.; Ji, X.; Keefer, L. K.; Saavedra, J. E. "Synthesis, mechanistic studies, and anti-proliferative activity of glutathione/glutathione S-transferase activated nitric oxide prodrugs" Bioorganic and Medicinal Chemistry 2008, 16, 9764-9771.
18) Chakrapani, H.; Goodblatt, M. G.; Udupi, V.; Malaviya, S.; Shami, P. J.; Keefer, L. K.; Saavedra, J. E. "Synthesis and In Vitro Anti-Leukemic Activity of Structural Analogues of JS-K, An Anti-Cancer Lead Compound" Bioorganic and Medicinal Chemistry Letters 2008, 18, 950-953.
19) Chakrapani, H.; Wilde, T. C.; Citro, M. L.; Goodblatt, M. G.; Keefer, L. K.; Saavedra, J. E. "Synthesis and Studies of Structural Analogues of PABA/NO, an Anti-Cancer Lead Compound" Bioorganic and Medicinal Chemistry 2008, 16, 2657-2664.
20) Chakrapani, H.; Showalter, B. M.; Citro, M. L.; Keefer, L. K.; Saavedra, J. E. "Nitric Oxide Prodrugs: Diazeniumdiolates of Hindered Secondary Amines" Organic Letters 2007, 9, 4551-4554.
21) Chakrapani, H.; Showalter, B. M.; Kong, L.; Keefer, L. K.; Saavedra, J. E. "V-PROLI/NO, a Prodrug of the Nitric Oxide donor, PROLI/NO" Organic Letters 2007, 9, 3409-3412.
22) Chakrapani, H.; Gorczynski, M. J.; King, S. B. "Allylic Nitro Compounds as Nitrite Donors" Journal of the American Chemical Society 2006, 128, 16332-16337.
23) Pamula, V. K.; Srinivasan, V.; Chakrapani, H.; Fair, R. B.; Toone, E. J. "A Droplet-based Lab-on-a-chip for Colorimetric Detection of Nitroaromatic Explosives" Proceedings of the 18th IEEE International Conference on Micro Electro Mechanical Systems 2005, 722-725.
24) Gooden, D. M.; Chakrapani, H.; Toone E. J. "C-Nitroso Compounds: Synthesis, Physicochemical Properties and Biological Activities" Current Topics in Medicinal Chemistry 2005, 5, 687-705.
25) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. "Enantioselective Cyclization/Hydrosilylation of 1,6-Enynes Catalyzed by a Cationic Rhodium Bis(phosphine) Complex" Organic Letters 2003, 5,157-159.
26) Wang, X.; Chakrapani, H.; Madine, J. M.; Keyerleber, M. A.; Widenhoefer, R. A. "Cyclization/ Hydrosilylation of Functionalized 1,6-Diynes Catalyzed by Cationic Platinum Complexes Containing Bidentate Nitrogen Ligands" The Journal of Organic Chemistry 2002, 67, 2778-2788.
27) Wang X.; Chakrapani, H.; Stengone C. N.; Widenhoefer R. A. "Synthesis of Carbobicyclic Compounds via Palladium-Catalyzed Cyclization/Hydrosilylation: Evidence for Reversible Silylpalladation" The Journal of Organic Chemistry 2001, 66, 1755-1760.